This book is hilarious, and you should read it for that reason. It's also thoughtful, ridiculous, insightful and self-deprecating, which makes it all the more enjoyable, even if it is written by an affluent, middle-aged, white man.

I can add this. Although the book is very much about Brookline and Brooklyn in contrast with Western Massachusetts and Maine, Hodgman describes so well what it is he sees in these places, it is likely you can think of places you can relate more closely to that embodies, e.g., the Maine-ness of Maine.